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Synfacts 2011(10): 1143-1143  
DOI: 10.1055/s-0030-1261089
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Epoxidation with a Chiral Metal-Organic Framework

Contributor(s): Yasuhiro Uozumi, Takao Osako
F. Song, C. Wang, W. Lin*
University of North Carolina, Chapel Hill, USA
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Publication History

Publication Date:
20 September 2011 (online)

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Significance

Chiral metal-organic framework (MOF) 1 was prepared by treatment of Mn-LH2 with Zn(NO3)2˙6H2O in a mixture of dibutylform­amide and EtOH (eq. 1). The chiral MOF 1 catalyzed the epoxidation of alkenes 3 with 2-(tert-butylsulfonyl)iodosylbenzene 2 to give the corres-ponding epoxides 4 in 60% to >99% conversion with 31-84% ee (eq. 2). In the formation of 4b, the catalyst was recovered by centrifugation and reused four times (4th run: 58% conversion, 64% ee).